The racemic N-benzylisothiazol-3-amine 1-oxide (2) was demonstrated to be an efficient partner in Diels-Alder reactions (Schemes 2-4) and a good dipolarophile in 1,3-dipolar cycloaddition reactions with nitrile oxides (Scheme 5). Polycyclic isothiazole S-oxides with different substitution patterns were obtained from 2 in good yield and in a fully regioselective way. Improved diastereoselection was observed performing the Diels-Alder or 1,3-dipolar cycloaddition reactions in H 2O.
Fused isothiazole S-oxide systems from cycloaddition reactions of N-benzylisothiazol-3-amine 1-oxide / F. Clerici, A. Casoni, A. Contini, M.L. Gelmi, S. Pellegrino. - In: HELVETICA CHIMICA ACTA. - ISSN 0018-019X. - 92:4(2009), pp. 779-789. [10.1002/hlca.200800342]
Fused isothiazole S-oxide systems from cycloaddition reactions of N-benzylisothiazol-3-amine 1-oxide
F. ClericiPrimo
;A. CasoniSecondo
;A. Contini;M.L. GelmiPenultimo
;S. PellegrinoUltimo
2009
Abstract
The racemic N-benzylisothiazol-3-amine 1-oxide (2) was demonstrated to be an efficient partner in Diels-Alder reactions (Schemes 2-4) and a good dipolarophile in 1,3-dipolar cycloaddition reactions with nitrile oxides (Scheme 5). Polycyclic isothiazole S-oxides with different substitution patterns were obtained from 2 in good yield and in a fully regioselective way. Improved diastereoselection was observed performing the Diels-Alder or 1,3-dipolar cycloaddition reactions in H 2O.
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